CA1069496A - Intermediaires pour la production de steroides a activite pharmaceutique - Google Patents

Intermediaires pour la production de steroides a activite pharmaceutique

Info

Publication number: CA1069496A
Authority: CA; Canada
Prior art keywords: group; process according; methyl; hydroxyl; alkyl
Prior art date: 1975-03-21
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA306,343A

Other languages

English (en)

Inventor

Frederick Cassidy

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Beecham Group PLC

Original Assignee

Beecham Group PLC

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1975-03-21

Filing date

1978-06-28

Publication date

1980-01-08

1975-03-21 Priority claimed from GB11819/75A external-priority patent/GB1538227A/en

1978-06-28 Application filed by Beecham Group PLC filed Critical Beecham Group PLC

1978-06-28 Priority to CA306,343A priority Critical patent/CA1069496A/fr

1980-01-08 Application granted granted Critical

1980-01-08 Publication of CA1069496A publication Critical patent/CA1069496A/fr

Status Expired legal-status Critical Current

Links

150000003431 steroids Chemical class 0.000 title abstract description 8
239000000543 intermediate Substances 0.000 title abstract description 4
150000001875 compounds Chemical class 0.000 claims abstract description 63
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 40
125000000217 alkyl group Chemical group 0.000 claims abstract description 24
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims abstract description 20
125000002252 acyl group Chemical group 0.000 claims abstract description 19
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 19
239000001257 hydrogen Substances 0.000 claims abstract description 19
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 12
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 8
125000005037 alkyl phenyl group Chemical group 0.000 claims abstract description 6
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims abstract description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims abstract description 5
125000003342 alkenyl group Chemical group 0.000 claims abstract description 3
125000004043 oxo group Chemical group O=* 0.000 claims abstract 9
125000006273 (C1-C3) alkyl group Chemical group 0.000 claims abstract 4
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract 2
238000000034 method Methods 0.000 claims description 45
230000008569 process Effects 0.000 claims description 38
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 29
238000006243 chemical reaction Methods 0.000 claims description 18
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 18
-1 acetoxy, propionyloxy, caproyloxy Chemical group 0.000 claims description 12
230000009467 reduction Effects 0.000 claims description 4
239000003153 chemical reaction reagent Substances 0.000 claims description 3
125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
230000010933 acylation Effects 0.000 claims description 2
238000005917 acylation reaction Methods 0.000 claims description 2
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 2
238000006266 etherification reaction Methods 0.000 claims description 2
150000004820 halides Chemical class 0.000 claims description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims 4
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims 3
AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 1
IVRMZWNICZWHMI-UHFFFAOYSA-N azide group Chemical group [N-]=[N+]=[N-] IVRMZWNICZWHMI-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
239000003098 androgen Substances 0.000 abstract description 12
238000002360 preparation method Methods 0.000 abstract description 6
230000001419 dependent effect Effects 0.000 abstract description 5
208000017520 skin disease Diseases 0.000 abstract description 3
MUMGGOZAMZWBJJ-DYKIIFRCSA-N Testostosterone Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 MUMGGOZAMZWBJJ-DYKIIFRCSA-N 0.000 description 36
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 27
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
229960003604 testosterone Drugs 0.000 description 18
239000000203 mixture Substances 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
241001465754 Metazoa Species 0.000 description 11
210000000056 organ Anatomy 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
239000007787 solid Substances 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
239000003208 petroleum Substances 0.000 description 7
241000700159 Rattus Species 0.000 description 6
230000002280 anti-androgenic effect Effects 0.000 description 6
230000000694 effects Effects 0.000 description 6
210000002374 sebum Anatomy 0.000 description 6
208000002874 Acne Vulgaris Diseases 0.000 description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 5
206010039792 Seborrhoea Diseases 0.000 description 5
206010000496 acne Diseases 0.000 description 5
239000000706 filtrate Substances 0.000 description 5
230000005764 inhibitory process Effects 0.000 description 5
150000002500 ions Chemical class 0.000 description 5
210000002307 prostate Anatomy 0.000 description 5
230000028327 secretion Effects 0.000 description 5
241000699800 Cricetinae Species 0.000 description 4
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
230000009102 absorption Effects 0.000 description 4
238000010521 absorption reaction Methods 0.000 description 4
229910052799 carbon Inorganic materials 0.000 description 4
150000001721 carbon Chemical group 0.000 description 4
OSVMTWJCGUFAOD-KZQROQTASA-N formestane Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)=O)[C@@H]4[C@@H]3CCC2=C1O OSVMTWJCGUFAOD-KZQROQTASA-N 0.000 description 4
150000002431 hydrogen Chemical class 0.000 description 4
230000002401 inhibitory effect Effects 0.000 description 4
229910052943 magnesium sulfate Inorganic materials 0.000 description 4
230000007935 neutral effect Effects 0.000 description 4
239000012074 organic phase Substances 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
230000001548 androgenic effect Effects 0.000 description 3
210000000918 epididymis Anatomy 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000009472 formulation Methods 0.000 description 3
210000004907 gland Anatomy 0.000 description 3
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000000047 product Substances 0.000 description 3
230000000699 topical effect Effects 0.000 description 3
ZXSQEZNORDWBGZ-UHFFFAOYSA-N 1,3-dihydropyrrolo[2,3-b]pyridin-2-one Chemical compound C1=CN=C2NC(=O)CC2=C1 ZXSQEZNORDWBGZ-UHFFFAOYSA-N 0.000 description 2
XVMSFILGAMDHEY-UHFFFAOYSA-N 6-(4-aminophenyl)sulfonylpyridin-3-amine Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=N1 XVMSFILGAMDHEY-UHFFFAOYSA-N 0.000 description 2
201000004384 Alopecia Diseases 0.000 description 2
BOJKULTULYSRAS-OTESTREVSA-N Andrographolide Chemical compound C([C@H]1[C@]2(C)CC[C@@H](O)[C@]([C@H]2CCC1=C)(CO)C)\C=C1/[C@H](O)COC1=O BOJKULTULYSRAS-OTESTREVSA-N 0.000 description 2
VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 2
102000004190 Enzymes Human genes 0.000 description 2
108090000790 Enzymes Proteins 0.000 description 2
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 2
WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 2
125000003668 acetyloxy group Chemical group [H]C([H])([H])C(=O)O[*] 0.000 description 2
238000005903 acid hydrolysis reaction Methods 0.000 description 2
230000001195 anabolic effect Effects 0.000 description 2
102000010640 androgen binding protein Human genes 0.000 description 2
108010077825 androgen binding protein Proteins 0.000 description 2
NXQOQNROJJFYCJ-FZFXZXLVSA-N androst-16-ene Chemical compound C1CCC[C@]2(C)[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 NXQOQNROJJFYCJ-FZFXZXLVSA-N 0.000 description 2
229960003473 androstanolone Drugs 0.000 description 2
150000001443 androstenes Chemical class 0.000 description 2
239000000051 antiandrogen Substances 0.000 description 2
230000037396 body weight Effects 0.000 description 2
125000004432 carbon atom Chemical group C* 0.000 description 2
229910052804 chromium Inorganic materials 0.000 description 2
239000011651 chromium Substances 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
239000006071 cream Substances 0.000 description 2
239000013078 crystal Substances 0.000 description 2
210000000172 cytosol Anatomy 0.000 description 2
238000006073 displacement reaction Methods 0.000 description 2
201000010063 epididymitis Diseases 0.000 description 2
238000001704 evaporation Methods 0.000 description 2
230000008020 evaporation Effects 0.000 description 2
238000002474 experimental method Methods 0.000 description 2
229910052736 halogen Inorganic materials 0.000 description 2
150000002367 halogens Chemical class 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
229910052744 lithium Inorganic materials 0.000 description 2
DVSDBMFJEQPWNO-UHFFFAOYSA-N methyllithium Chemical compound C[Li] DVSDBMFJEQPWNO-UHFFFAOYSA-N 0.000 description 2
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
239000002674 ointment Substances 0.000 description 2
230000003647 oxidation Effects 0.000 description 2
238000007254 oxidation reaction Methods 0.000 description 2
230000000144 pharmacologic effect Effects 0.000 description 2
125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
210000001732 sebaceous gland Anatomy 0.000 description 2
LKZMBDSASOBTPN-UHFFFAOYSA-L silver carbonate Substances [Ag].[O-]C([O-])=O LKZMBDSASOBTPN-UHFFFAOYSA-L 0.000 description 2
229910001958 silver carbonate Inorganic materials 0.000 description 2
229910000104 sodium hydride Inorganic materials 0.000 description 2
239000012312 sodium hydride Substances 0.000 description 2
230000000638 stimulation Effects 0.000 description 2
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
150000003573 thiols Chemical class 0.000 description 2
VBAFPUVFQZWOJM-MHJRRCNVSA-N (8r,9r,10s,13r,14s)-13-methyl-1,2,3,4,5,6,7,8,9,10,11,12,14,15-tetradecahydrocyclopenta[a]phenanthrene Chemical compound C1CCC[C@@H]2[C@H]3CC[C@](C)(C=CC4)[C@@H]4[C@@H]3CCC21 VBAFPUVFQZWOJM-MHJRRCNVSA-N 0.000 description 1
YQACAXHKQZCEOI-SCZYCMLPSA-N (8s,9s,10r,13s,14s)-10,13-dimethyl-3-oxo-1,2,6,7,8,9,11,12,14,15,16,17-dodecahydrocyclopenta[a]phenanthrene-17-carboxylic acid Chemical compound O=C1CC[C@]2(C)[C@H]3CC[C@](C)(C(CC4)C(O)=O)[C@@H]4[C@@H]3CCC2=C1 YQACAXHKQZCEOI-SCZYCMLPSA-N 0.000 description 1
NVKAWKQGWWIWPM-ABEVXSGRSA-N 17-β-hydroxy-5-α-Androstan-3-one Chemical compound C1C(=O)CC[C@]2(C)[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CC[C@H]21 NVKAWKQGWWIWPM-ABEVXSGRSA-N 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
206010002091 Anaesthesia Diseases 0.000 description 1
241000220438 Arachis Species 0.000 description 1
235000003911 Arachis Nutrition 0.000 description 1
102000014914 Carrier Proteins Human genes 0.000 description 1
206010020112 Hirsutism Diseases 0.000 description 1
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 1
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
241000699670 Mus sp. Species 0.000 description 1
QGMRQYFBGABWDR-UHFFFAOYSA-M Pentobarbital sodium Chemical compound [Na+].CCCC(C)C1(CC)C(=O)NC(=O)[N-]C1=O QGMRQYFBGABWDR-UHFFFAOYSA-M 0.000 description 1
239000002202 Polyethylene glycol Substances 0.000 description 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
239000005864 Sulphur Substances 0.000 description 1
206010070863 Toxicity to various agents Diseases 0.000 description 1
IATKKATWPOVYCC-VXEDDEPTSA-N [2H]C1(C[C@H]2[C@@H]3CCC4=CCCC[C@@]4([C@H]3CC[C@@]2(C1)C)C)[2H] Chemical compound [2H]C1(C[C@H]2[C@@H]3CCC4=CCCC[C@@]4([C@H]3CC[C@@]2(C1)C)C)[2H] IATKKATWPOVYCC-VXEDDEPTSA-N 0.000 description 1
125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 description 1
239000012346 acetyl chloride Substances 0.000 description 1
239000002253 acid Substances 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001263 acyl chlorides Chemical class 0.000 description 1
150000001350 alkyl halides Chemical class 0.000 description 1
238000001949 anaesthesia Methods 0.000 description 1
230000037005 anaesthesia Effects 0.000 description 1
206010068168 androgenetic alopecia Diseases 0.000 description 1
201000002996 androgenic alopecia Diseases 0.000 description 1
229940030495 antiandrogen sex hormone and modulator of the genital system Drugs 0.000 description 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
150000001540 azides Chemical class 0.000 description 1
230000008901 benefit Effects 0.000 description 1
108091008324 binding proteins Proteins 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
239000002775 capsule Substances 0.000 description 1
125000006243 carbonyl protecting group Chemical group 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
210000004027 cell Anatomy 0.000 description 1
230000001413 cellular effect Effects 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
230000002860 competitive effect Effects 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000002537 cosmetic Substances 0.000 description 1
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 1
230000002939 deleterious effect Effects 0.000 description 1
208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 1
238000001035 drying Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
229940093476 ethylene glycol Drugs 0.000 description 1
239000000834 fixative Substances 0.000 description 1
125000000268 heptanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
238000010562 histological examination Methods 0.000 description 1
150000002430 hydrocarbons Chemical group 0.000 description 1
238000005984 hydrogenation reaction Methods 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
238000000338 in vitro Methods 0.000 description 1
208000015181 infectious disease Diseases 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
239000010410 layer Substances 0.000 description 1
239000012280 lithium aluminium hydride Substances 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
150000004702 methyl esters Chemical class 0.000 description 1
125000000896 monocarboxylic acid group Chemical group 0.000 description 1
210000003205 muscle Anatomy 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229960004719 nandrolone Drugs 0.000 description 1
NPAGDVCDWIYMMC-IZPLOLCNSA-N nandrolone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@H](CC4)O)[C@@H]4[C@@H]3CCC2=C1 NPAGDVCDWIYMMC-IZPLOLCNSA-N 0.000 description 1
CMWTZPSULFXXJA-VIFPVBQESA-N naproxen Chemical group C1=C([C@H](C)C(O)=O)C=CC2=CC(OC)=CC=C21 CMWTZPSULFXXJA-VIFPVBQESA-N 0.000 description 1
229940105631 nembutal Drugs 0.000 description 1
239000012299 nitrogen atmosphere Substances 0.000 description 1
239000003883 ointment base Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
239000007800 oxidant agent Substances 0.000 description 1
229910052760 oxygen Inorganic materials 0.000 description 1
239000001301 oxygen Substances 0.000 description 1
229910052763 palladium Inorganic materials 0.000 description 1
239000008194 pharmaceutical composition Substances 0.000 description 1
229920001223 polyethylene glycol Polymers 0.000 description 1
LJCNRYVRMXRIQR-OLXYHTOASA-L potassium sodium L-tartrate Chemical compound [Na+].[K+].[O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O LJCNRYVRMXRIQR-OLXYHTOASA-L 0.000 description 1
229940074439 potassium sodium tartrate Drugs 0.000 description 1
239000000843 powder Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
210000001625 seminal vesicle Anatomy 0.000 description 1
235000011006 sodium potassium tartrate Nutrition 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
239000006228 supernatant Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
235000020357 syrup Nutrition 0.000 description 1
239000006188 syrup Substances 0.000 description 1
239000003826 tablet Substances 0.000 description 1
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
210000001541 thymus gland Anatomy 0.000 description 1
231100000419 toxicity Toxicity 0.000 description 1
230000001988 toxicity Effects 0.000 description 1
201000010653 vesiculitis Diseases 0.000 description 1
238000005303 weighing Methods 0.000 description 1

Landscapes

Steroid Compounds (AREA)

CA306,343A 1975-03-21 1978-06-28 Intermediaires pour la production de steroides a activite pharmaceutique Expired CA1069496A (fr)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
CA306,343A CA1069496A (fr)	1975-03-21	1978-06-28	Intermediaires pour la production de steroides a activite pharmaceutique

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
GB11819/75A GB1538227A (en)	1975-03-21	1975-03-21	16,16-disubstituted steroids of the androstene series
CA248,260A CA1069498A (fr)	1975-03-21	1976-03-19	Steroides a activite pharmaceutique
CA306,343A CA1069496A (fr)	1975-03-21	1978-06-28	Intermediaires pour la production de steroides a activite pharmaceutique

Publications (1)

Publication Number	Publication Date
CA1069496A true CA1069496A (fr)	1980-01-08

Family

ID=27164379

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA306,343A Expired CA1069496A (fr)	1975-03-21	1978-06-28	Intermediaires pour la production de steroides a activite pharmaceutique

Country Status (1)

Country	Link
CA (1)	CA1069496A (fr)

1978
- 1978-06-28 CA CA306,343A patent/CA1069496A/fr not_active Expired

Legal Events

Date	Code	Title	Description
1997-01-08	MKEX	Expiry

Publication	Publication Date	Title
US4344941A (en)	1982-08-17	Antiandrogenic 17α-substituted steroids
CA2023008C (fr)	2001-05-15	17 .beta.-(cyclopropyloxy)androst-5-en-3 .beta.-ol substitue en position4 et composes apparentes utiles comme inhibiteurs de la c17-20 lyase
CA1173431A (fr)	1984-08-28	10-alcynyl-steroides
CA1069498A (fr)	1980-01-08	Steroides a activite pharmaceutique
US4891367A (en)	1990-01-02	17β-(cyclopropyloxy)androst-5-en-3β-ol and related compounds useful as C17-20 lyase inhibitors
CA1069496A (fr)	1980-01-08	Intermediaires pour la production de steroides a activite pharmaceutique
CA2086678A1 (fr)	1992-01-05	Steroides [3,2-c]pyrazole et [3,2-d]triazole anti-androgeniques
WO1993013122A1 (fr)	1993-07-08	3-methylsulfonylhydrazono- et 3-oxyimino-steroides, leur procede de fabrication, preparations pharmaceutiques renfermant ces steroides et leur utilisation dans la fabrication de medicaments
EP0289451B1 (fr)	1993-10-27	3-Méthylène-androst-4-ène-17-ones, procédé de préparation et compositions pharmaceutiques les contenant
US3954805A (en)	1976-05-04	Process for preparing zearalene type compounds
EP0062903A1 (fr)	1982-10-20	17-Alpha-alkyl-17 bêta-hydroxy-1-alpha-méthyl-4-androstène-3-ones, procédé pour les préparer, et préparations pharmaceutiques les contenant
JPS6362515B2 (fr)	1988-12-02
EP0225272B1 (fr)	1989-04-05	1-Méthyl-15alpha-alkyl-androsta-1,4-diène-3,17-diones, leur procédé de préparation et préparations pharmaceutiques les contenant
CA1244404A (fr)	1988-11-08	17- (thio substitue)-17-(dithio substitues) androstenes
US3676502A (en)	1972-07-11	BENZ {21 a{22 {0 ANTHRACENE STEROID ANALOGUE
US3450720A (en)	1969-06-17	3-difluoromethylene steroids
CA1101409A (fr)	1981-05-19	Traduction non-disponible
US3452060A (en)	1969-06-24	17-hydroxy-17-(3-oxo-1-propynyl or-propenyl) steroids
US4871725A (en)	1989-10-03	1-methyl-15α-(1-oxyalkyl)androsta-1,4-diene-3,17-diones, processes for their production, and pharmaceutical preparations containing them
DE10056675A1 (de)	2002-05-16	Verfahren zur Herstellung von 4-(17alpha-Methylsubstituierten 3-Oxoestra-4,9-dien-11ß-yl)-benzaldehyd-(1E oder 1Z)-oximen
US3105069A (en)	1963-09-24	16, 17-cyclic acetals of 16 beta-mercapto-17 beta-hydroxy estrogen derivatives and intermediates in the preparation thereof
CH557805A (de)	1975-01-15	Verfahren zur herstellung von oestra-1,3,5(10),7-tetraenen.
EP0218647A1 (fr)	1987-04-22	Agents de traitement dermatologique.
CA1094050A (fr)	1981-01-20	Procede de production de nouvelles gona-4,9(10)- dienes
DE2527311A1 (de)	1976-01-08	7a-hydroxy-19-norpregn-4-en-3,20- dion-derivate, verfahren zu ihrer herstellung und sie enthaltende pharmazeutische mittel